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Gregory Pepper and His Problems is an unusual, musical fella. I don't know him personally, but I was sent this picture of him and his cat, and his song topics range from being a john, to a fairly descriptive - and possibly accurate - song about building a boat. It's tough to pigeonhole his style of music, so I won't bother.

With two upcoming Toronto shows -- November 5th at Kensington's Teranga and November 7th at the Mod Club -- with the Islands, I decided to give Gregory (which is not his real name) a inquisitive phone call...

He released his third full-length, With Trumpets Flaring, under the moniker Gregory Pepper and His Problems this summer and since then he's been very, very busy doing all kinds of music. He told me that there was a period of time, between this record in the last, where he completely gave up on music.

"I guess like anybody else you just have that animosity just below the surface, serving hot dogs on a stick, or whatever people do. When I moved back to Guelph [after school] I went crazy and thought I was going to be a carpenter for... like... a year. I stopped playing music and thought I was going to work with wood. It turned out I wasn't very good at it and I didn't really enjoy it either. I'm too soft. I had very little in common with the average blue-collar worker. I felt very much like a fish-out-of-water in that situation."

I would describe a lot of the lyrical content of his songs as melodramatic, so my first question was whether or not he was an everyday melodramatic person.

"I don't suppose so, possibly not. I think music should be like that, or art should be like that. It should be the height of depression or the height of elation, but I think I'm even temperate in real life; probably to the point where my presence is boring for those in the same room as me... so I try to compensate for that on my records."

Despite the impression that his record might make on listeners, Gregory is actually a huge fan of hip-hop and is actively involved in that scene as well. In fact, if you listen closely to his new record, there are traces of his interest in the genre.

"I do production and I do a lot of freelance recording on a lot of different hip-hop tunes. Vocals or instruments, bass, and I do beats as well. On my record, I would say about a third of the songs have programmed drums and there's sampling as well."

I had to ask about his lyrics. Seriously, where are these ideas coming from?

"I don't like to be too serious - on all levels of music. I just don't want to hear it. I like to keep a tongue-and-cheek element to it. I like to avoid writing in first-person, if at all possible. I'll write the melody before the lyrics and I generally have dummy lyrics to go with it, and sometimes those stick. That's why I could never be a real rapper; those guys have a lot to say, and I don't really have any strong opinions about anything. There are certain words I try to avoid as well. I made the conscious decision not to say the word 'heart' anymore. All that broken heart bullshit is so fucking boring - I added that to may list. I phased it right out."

A lot of artists and musicians, at some point will move to a bigger city, closer to the venues, closer to other bands, possibly closer to opportunity. Gregory doesn't care about those things.

"I'm kind of an anxious sort when I'm in the big city. I can take it for a weekend. It's all concrete, it's all hard, and my dog will only take a shit on that strip of grass between the sidewalk and the street and you guys don't have that. Your side walks ends at the street."

I insisted that his dog would adjust...

"No! He's like me. He's stubborn and melodramatic! I only shit in my own backyard! Now you'll probably sell this to some scat-blog, the one that'll only be in print in Germany."